Palladium-catalyzed difunctionalization/dearomatization of N-benzylacrylamides with α-carbonyl alkyl bromides: facile access to azaspirocyclohexadienones. Issue 35 (31st August 2021)

• Record Type: Journal Article
• Authors: Peng, Chuan-Chong; Wu, Li-Jun; Pi, Shao-Feng
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 35(2021)
• Page Start: 7602
• Page End: 7606
• Publication Date: 2021-08-31
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01405f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient palladium-catalyzed difunctionalization/dearomatization of N -benzylacrylamides with α-carbonyl alkyl bromides for the preparation of azaspirocyclohexadienones has been disclosed. Abstract : An efficient palladium-catalyzed difunctionalization/dearomatization of N -benzylacrylamides with α-carbonyl alkyl bromides as alkyl radical precursors has been described. Various α-carbonyl alkyl bromides, including α-bromoalkyl esters and ketones, reacted smoothly to provide important azaspirocyclohexadienones in moderate to excellent yields. In addition, mechanistic studies suggested that the reaction proceeded via a radical pathway.